Dextro-rotary glaucine or d-glaucine hydrobromide has been used as an antitussive agent. D-glaucine can be isolated from the yellow poppy. The racemate, d,l-glaucine can be synthesized from papaverine, following the procedure of Frank and Tietze, Angewandte Chemie (1967) pp 815-6, or Helm, Belgian Pat. No. 866,079, and the racemate can be resolved with d-tartaric acid as disclosed by the above mentioned Helm Belgian patent. A variety of other preparative procedures are also known. Chan and Maitland, J. Chem. Soc. (C) 1966, 753; and Cava, et al. J. Org. Chem. 35, 175 (1970). Separation of the isomers has been carried out by conventional procedures, such as using d- or 1-tartaric acid to form the d- or 1-bitartrate salts and separating the salts by fractional crystallization.
Glaucine has the structure ##STR1## and is thus structurally somewhat related to other plant alkaloids such as codeine and aporphine. D,L-Glaucine, unlike codeine, forms a phosphate salt with about one and one-half molar proportions of phosphoric acid, as disclosed in the above-cited Wang application.